


A Winchester Always Pays His Debts

by lightsaroundyourvanity



Category: Supernatural
Genre: Episode: s05e03 Free to Be You and Me, First Time, M/M
Language: English
Status: Completed
Published: 2013-05-03
Updated: 2013-05-03
Packaged: 2017-12-10 06:25:38
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,070
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/782852
Author URL: https://archiveofourown.org/users/lightsaroundyourvanity/pseuds/lightsaroundyourvanity
Summary: <blockquote class="userstuff">
              <p>The whole brothel thing might not have worked out, but Dean still wants to take a shot at swiping Castiel's V, once and for all.</p>
            </blockquote>





	A Winchester Always Pays His Debts

**Author's Note:**

> Oh hey, I haven’t done destiel in awhile. Call this my smutty what-if to the infamous brothel scene in 5x03. Every spn fic writer gets one, right?

It starts with a promise, that grows into an obsession, and soon it’s all Dean can goddamn think about: while he’s brushing his teeth, while he grabs breakfast at a diner with Sam, while he’s ganking monsters in dirty small towns that only hunters and crazy people would ever bother to visit.  
  
 _There are two things that I know for certain: One, Burt and Ernie are gay. And two, you are not gonna die a virgin. Not on my watch._  
  
Of course then everything had gone hilariously wrong, and Cas hadn’t even died the next day, so Dean had chalked it all up to missed chances and soldiered on, chasing omens and hunting Lucifer and watching out for Sam. You know. Run-of-the-mill kind of stuff.  
  
Except he really can’t stop thinking about it, and even though Dean knows that there are bigger fish to fry (the apocalypse and all), and that it’s a little weird to be this preoccupied with your best friend’s virginity, he can’t help himself. After all, Cas could die any day now (not that he likes thinking about this, but let’s be honest: any of them could), and he’d die with his virginity still intact. Dean thinks that this is unacceptable in any circumstance, but for a dude as cool as Castiel, it’s a downright crime.   
  
Besides, he had promised.  
  
When a case takes them to Nevada, Dean can’t believe his luck. He’d almost say it was destiny, but he’s not on great terms with the word lately, and anyway, a vampire nest holed up up in Las Vegas isn’t preordained so much as it’s a pack of monsters following the food. But still, he and Sam so rarely end up in big cities, and Dean recognizes a golden opportunity when he sees one. He begins to come up with a plan.  
  
He thinks that it’s a pretty good plan, too, although when he brings up the idea with Sam, his brother shakes his head and looks at him like he’s gone crazy.  
  
“You want to hire Cas an escort.” Sam says incredulously.  
  
“What’s wrong with that?” Dean asks, a little defensively.   
  
“An _escort_.”  
  
“Well, it’s not like we can just take him out on the town. Dude’s got no game.”  
  
“Because paying a woman to have sex with Cas worked out so well the last time you tried it,” Sam points out.  
  
“It’ll be different this time,” says Dean.   
  
“Oh yeah?” Sam takes a casual drink from his kale smoothie, and Dean suppresses a shudder. It looks radioactive.   
  
“Yeah. I’m gonna stay in the room. Make sure Cas doesn’t fuck anything up this time.”  
  
Sam all but chokes on his smoothie. “You’re going to… stay in the room? The whole time?”  
  
Dean shrugs. “Sure, why not?”  
  
“You don’t think that sounds incredibly awkward?”  
  
Dean starts to shrug again, and then stops himself. Would it be? Maybe he hasn’t thought this through. But sex is nothing new to him, and he figures that since he’s paying for it, it isn’t as though he’ll risk peering into some intimate moment of Castiel’s. And besides, Cas rebuilt him from the soul up. Dean thinks that more than makes up for catching an eyeful of full frontal vessel.  
  
Then he starts to think of what else he might witness. Full frontal vessel nudity is a given. But there’s also the curve of a hipbone, and blue eyes with their pupils blown wide, and a gravelly voice unstrung with pleasure and… fuck. Dean is beginning to see how things might get awkward. “Maybe I can duck out when it looks like things are heading in the right direction,” he mumbles, running a hand through his hair.  
  
Sam smirks, and slurps on his smoothie. Dean wants to tell him that it looks like pond scum, but suddenly, he has way too much to think about.  
  
+_+_+_+  
  
It’s not awkward. It’s not awkward unless he lets it be awkward. This is what Dean tells himself as he paces his empty motel room, waiting for a knock on the door. With Sam’s help, he had managed to find a girl that fit his unique specifications. Sam had cleared out soon after, remarking that some things he would rather leave to his imagination, and Dean had sneered at him. And then he had waited.  
  
When the knock comes, Dean springs about a foot in the air, and then chastises himself for being a baby. He smooths down his hair and goes to answer the door.  
  
The service had said her name was Astrid, and well, she _looks_ like an Astrid, leggy and blond, even though Dean knows that there is no way it’s her real name. Her lips are coated with some frosted pink goo that Dean immediately hates, but since it’s not for him he tries not to worry about it.    
  
“Dean Winchester?” Astrid purrs, and she sounds confident. That’s good, Dean thinks. Cas needs someone who can show him around, and who won’t spook at the first sign of his angel crap. Dean thinks that this chick might work.  
  
Astrid steps into the room and looks around. “I thought this was a party for three?”  
  
Dean swallows. Right. Time to get Cas. Admittedly, this is the part of his plan that he put the least amount of thought into, but he thinks he can make it work. “It is,” he assures her. “I just have to… uh, I just have to get my friend. Hold tight for a minute, okay?”  
  
Astrid looks him up and down, but doesn’t say anything other than, “Sure, sweetheart,” and for one maddening minute Dean worries that she thinks he is the virgin and that his “friend” will mysteriously not show up. Irrationally, Dean is offended. Does he _look_ like a virgin?  
  
As soon as the door clicks shut, Dean whips out his cell and calls Castiel.   
  
He answers on the second ring. “What is it, Dean?”  
  
Dean finds that his mouth has gone dry. “I’m at the Dharma Motel in Vegas,” he blurts. “Room 4B. Can you—”  
  
Before Dean can even finish his sentence, Castiel arrives in a ruffle of wingbeats. He snaps his phone shut. “I’m here.”  
  
“You’re here,” says Dean, looking Castiel up and down.   
  
“Yes, that’s what I just said.”  
  
“You— I got you something.” Inwardly, Dean cringes. Could that have come out any douchier?  
  
Castiel looks surprised, even a touch pleased. “Oh?”  
  
“It’s a woman. You know… an escort.” And just like that, Dean realizes that yeah, he could have sounded douchier, and he just did.  
  
The surprise stays, but any hint of a pleased expression drains right out of Castiel’s face. “Dean, we don’t have time for this,” he says tightly.  
  
“Oh come on,” Dean replies. “The apocalypse will still be there tomorrow.”  
  
“Precisely. The _apocalypse_.”  
  
“Come on,” Dean says again. “A promise is a promise.”  
  
“I’ll let it go,” Cas says stiffly, and there’s a nervousness to him that Dean recognizes all too well from the brothel in Kansas City.  
  
“You will,” Dean agrees, “Let go. Go on inside, Cas. It’s not polite to keep a lady waiting.”  
  
A look of fleeting panic crosses Castiel’s face, but he lets Dean nudge him towards the door, and then through it.  
  
Astrid was reclined on the bed now, propped up on her elbows, her long legs crossed in front of her. Those frosted pink lips quirk up in a smirk when Castiel shuffles through the door, and Dean notices her eyes run over Castiel in an approving, hungry way that makes his stomach clench defensively. Yeah, he knows what Astrid is here for (hell, he paid for it), but something about her appraising glance has turned sour in his mouth. Like, she doesn’t know Cas; so she should stop looking at him like she does.   
  
Since it’s a totally irrational, out-of-the-blue feeling, and he is here to help out a buddy, Dean does his best to push it aside and plasters a grin to his face. “He’s all yours, sweetheart,” he says, with more bravado than he feels.  
  
Astrid unfolds herself from the bed and saunters towards Castiel until she is right up in his personal space, still looking him up and down like he is a choice cut of meat. “You must be Cas.”  
  
Castiel gulps. “Hello.”  
  
Astrid catches hold of Castiel’s tie and leans close to murmur in his ear. “I don’t usually say this,” she tells him, “But you can kiss me if you’d like.”  
  
Castiel doesn’t move, doesn’t even respond to the way that Astrid is fiddling with his tie and speaking breathily into his ear. Instead, he offers a very stiff, very formal, “Thank you.”  
  
When Castiel makes no further movement, Dean clears his throat. “Uh… you’re supposed to kiss her, Cas,” he says, gesturing to the escort that was pressing herself obscenely close to Castiel now.  
  
“Oh.” Despite his compromised position, Castiel’s eyes immediately seek out Dean’s, and he tilts his head to one side. “Show me.”  
  
“Uh…” Dean is at a loss. No way had he considered himself an active participant in this crazy night, by any stretch of the imagination. But then he thinks, hey, this is the guy’s first time, and he doesn’t blame him for needing a few pointers. He walks over to Castiel, gently pries Astrid away from him, and presses his mouth to those awful, goopy looking pink lips, feels them give and part beneath his own instantly. Dean feels the tip of Astrid’s tongue touch his own, and then he is suddenly yanked away, Castiel’s hand rough on his shoulder.  
  
“No, Dean.” he didn’t move his hand. “Show _me_.”  
  
As soon as Dean gets what Castiel means, his eyes flash straight to his lips. They look full and dry, and are slightly, _slightly_ parted, and Dean feels his throat constrict. This had to be going beyond the call of duty. But on the other hand…  
  
Who was he to start drawing lines in the sand? And hey, didn’t he hear that it’s not gay if it’s in a three way? Dean licks his lips, tasting artificial strawberries, and then crushes his mouth to Castiel’s.   
  
Castiel ignites. He threads his hands behind Dean’s neck and forces his mouth open, licks his way inside even as he starts walking backwards. And it’s not until Castiel has backed them into the bed and sat down, ushering Dean to stand between his knees, that Dean realizes that Castiel had been totally full of shit with his blushing angel act, and it makes him want to laugh, even as it sparks something needy and electric inside him. Dean cups Castiel’s face in his hands and kisses him for all he is worth, rolling his tongue against Castiel’s, coaxing a soft groan from the back of his throat.   
  
Dean isn’t sure how long they kiss for, but it must be awhile, because dimly, he registers Astrid coughing in the background.  
  
“Should I go?” she asks pointedly.  
  
Castiel peers at her over Dean’s shoulder, very matter-of-factly. “Probably,” he admits, and then he captures Dean’s mouth with his own again. And Dean doesn’t even care if it’s rude: he kisses Castiel back, and in the background he can hear an aggrieved huff, and then the slam of the door. When Dean starts at the noise, Castiel tugs him closer by his jacket and kisses him deeper. He leans back, pulling Dean on top of him, and even though a big chunk of Dean is thinking _oh yeah_ right now, another part of him is still pretty rattled, and it is because of that part of him that he _does_ break apart from Castiel, props himself up so he can look the angel in the face.   
  
“Cas, what are we doing?”  
  
Castiel looks up at Dean through eyes that are half lidded. “You made me a promise, Dean.”  
  
Of course he had, but he hadn’t meant this, and the part of him that wants this –has probably wanted it for awhile– is frankly freaking him out a little bit right now. “What about the apocalypse?”  
  
“Screw the apocalypse,” Cas growls, and the part of Dean’s brain that is freaking out shuts down, because he has better things to do when there is a hot angel wriggling beneath him. He lowers his head to mouth at Castiel’s jawline, bites down gently on his earlobe, revels in the breathy noises he is drawing from Cas. Castiel pushes at Dean’s jacket until Dean can shrug it off, and the button down he is wearing underneath comes off shortly afterwards. When Dean sits up to pull his t-shirt over his head Castiel makes a noise of protest, so Dean dips down and kisses Castiel again, hungrily and without artistry, their teeth clicking together as Dean sucks on Castiel’s tongue. He is pulling frantically on Castiel’s tie now and trying to undo shirt buttons at the same time, suddenly desperate to have Castiel without eleven layers on him. Finally, he just rips the shirt open, buttons clicking at they scatter on the motel room’s tile floor. Castiel gets the idea and sits up long enough to pull off his overcoat and suit jacket and ruined shirt and throw them in a crumpled heap onto the floor.  
  
“That was unnecessary,” Castiel comments.   
  
“This is unnecessary,” Dean retorts, pulling loose Castiel’s tie and letting it flutter to the ground with the rest of his clothes. He lays his hands on Castiel’s bare chest and pushes him flat on his back again, runs his tongue down the side of Castiel’s neck and tastes salt and skin. Dean kisses his way down Castiel’s chest, pausing only when he reaches the top button of Castiel’s slacks. Castiel raises his hips, urging Dean onward, and fuck, if that wasn’t a green light, Dean doesn’t know what is, so he undoes the button and pulls the zipper down, and lets Castiel’s hard cock spring free.  
  
The first taste of Castiel’s cock is heavy and salty against Dean’s tongue. The whining moan it pulls from Castiel is beyond delicious. Encouraged and incredibly turned on, Dean swirls his tongue around the head of Castiel’s cock, and then swallows it down until it bumps the back of his throat, his tongue rolling against the shaft on the way down. Castiel groans and the overhead lights spark. He bunches his hands in Dean’s hair, his grip all-but-painful, one leg flung over Dean’s shoulder once he kicks off his pants. Dean continues to suck on Castiel, making sloppy, wet noises. His hand slips over Castiel’s balls and rolls them together once before straying further back. His thumb presses against the sensitive patch of skin between Castiel’s balls and his ass and Dean feels the muscles in Castiel’s thighs jump.   
  
“Dean,” Castiel groans. “I want you–I want you to–”  
  
A wrecked noise escapes Dean and he comes off Castiel’s dick with a loud pop, and then he licks a long stripe down Castiel’s length, not stopping until he is tonguing the entrance of Castiel’s hole. Castiel shifts his other leg over Dean’s shoulder to give him better access, and Dean flicks his tongue against Castiel’s hole, urging the puckered ring of muscle to relax. He brings two fingers to his mouth and sucks them wet before pushing them inside Castiel, feeling the angel clench, and then ease to accommodate him. Dean moves his fingers inside Castiel, slowly at first, and then speeding up and adding a third as he feels Castiel’s ass loosen.  
  
“Dean,” Castiel gasps, “ _Please_.”  
  
Dean doesn’t need to be told twice. He sits up and unbuckles his belt, eyes on Castiel as he unsnaps the button of his jeans and pushes them down. His cock is so hard its aching, the head already leaking, and the hungry, adoring look in Castiel’s eyes pushes him even closer to a lusty precipice. Dean wriggles out of his jeans and braces himself over Castiel, Castiel’s legs slung over his shoulders again. The blunt head of Dean’s cock nudges against Castiel’s entrance and he pushes himself in, inch by torturous inch, until he is buried to the hilt and surrounded by the hot, tight feeling of Castiel.  
  
Castiel sighs, and Dean begins to move.   
  
Slowly, at first, his hips rocking against Castiel, their eyes locked on one another. And then faster, more urgent, as Dean feels himself racing closer and closer towards orgasm. A snap of his hips, and Dean’s cock scrapes against Castiel’s prostate, making Castiel cry out. Dean reaches between them and wraps his hand around Castiel’s cock, milks it in his fist until he feels the first sticky spurts of semen as Castiel comes, Dean’s name a stuttered litany on his lips. Between watching Castiel come undone beneath him and the tight, awesome pleasure of fucking Castiel’s ass, Dean knows that he is about to blow too, and he thrusts deep when he comes inside Castiel with a shout.  
  
For a minute afterwards, neither of them speak. They stare at each other, breathing hard, until Dean pulls out and collapses against Castiel, his chin resting on Castiel’s chest.  
  
Dean lets out a breath. “That was–”  
  
Castiel’s answering chuckle is low and breathless. “Yeah.”  
  
Dean is about to say something else, or at least he thinks he is, but he can already feel himself beginning to doze off in a haze of post-sex endorphins. The last he remembers before falling asleep is Castiel’s arm slipping up to circle his waist.  
  
 Dean isn’t sure how long he sleeps for. Too long. He is woken by the rattle of the doorknob, and the choked, indignant noise that Sam makes upon walking in on his brother naked and entwined with an angel of the lord.  
  
“Aw, _Dean_!” Sam cries. “At least put a sock on the door!”  
  
Dean is up like a shot, yanking the bedsheets around his waist. His eyes meet Castiel’s in a panic, and Cas looks from Dean, to Sam, and back to Dean again. He gulps, and then gives Dean the tiniest of shrugs before vanishing in a flutter.  
  
“Son of a–” Dean swears, and wraps the sheet tighter around himself. “Frigging angels,” he mutters, but there is a giddy trace of fondness to it.  
  
“An escort, huh,” says Sam.  
  
“Shut up,” Dean snaps. He glares at Sam, but quickly ducks his head, unable to hide a stupid grin. “I improvised.”


End file.
